Succinimide compounds and use thereof

ABSTRACT

Provided are a borosuccinimide compound obtained through reaction of (a) a succinic acid/anhydride substituted with an alkyl or alkenyl group having a number-average molecular weight of from 200 to 5,000, (b) a polyalkylene-polyamine of which at least 5 mol % has a terminal cyclic structure, and (c) a boron compound; and a succinimide compound obtained through reaction of (A) a succinic acid/anhydride substituted with an alkyl or alkenyl group having a molecular weight of from 200 to 5,000, with (D) a hydrocarbon-substituted polyalkylene-polyamine. These compounds are stable even at high temperatures and have good high-temperature detergency, and they are useful for ashless detergent dispersants having the ability to disperse fine particles. Also provided are a mixture of any of these compounds and a specific ester derivative; a lubricant additive and a fuel oil additive comprising the mixture as the essential ingredient; and a lubricant and a fuel oil composition containing the additive.

TECHNICAL FIELD

The present invention relates to novel succinimide compounds and theiruse, precisely to novel succinimide compounds useful for lubricants anddetergent dispersants for fuel oil, to a lubricant additive and a fueloil additive comprising the compound as the essential ingredient, and toa lubricant composition and a fuel oil composition.

BACKGROUND ART

Succinimides and hydroxybenzylamines are generally known forconventional ashless dispersants. Owing to their specific ability todisperse fine particles, the compounds have heretofore been widely usedfor lubricant additives for gasoline engine oil, diesel engine oil, and2-cycle engine oil. In addition, since their synergistic effect withzinc dialkyldithiophosphates, metal detergents of the like is consideredgood, the compounds are one group of extremely important lubricantadditives. However, it is often said that they are unstable at hightemperatures and their detergency at high temperature is notsatisfactory.

For example, JP-B 43631/1971 discloses reaction products obtainedthrough reaction of a reaction intermediate of alkylphenol, formaldehydeand polyalkylene-polyamine with a polyalkenylsuccinic anhydride, andreaction products obtained through further reaction of that reactionproduct with a boron-containing compounds, saying that those reactionproducts are effective for oxidation-stable, ashless detergentdispersants and that they have improved oil-solubility. JP-A 8304/1976discloses reaction products obtained through reaction of a reactionintermediate of polyalkenylsuccinic acid (anhydride) andpolyalkylene-polyamine with an aromatic alcohol (e.g., alkylphenol,phenol, thiodiphenol) in the presence of aldehyde. However, thesereaction products are still unsatisfactory in point of their stabilityat high temperatures.

JP-A 168492/1988 discloses reaction products like in JP-B 43631/1971,for which, however, used is glycolic acid as the reactant and not aboron-containing compound. As in the prior-art references, however, thereaction products are also unsatisfactory in point of their stability athigh temperatures.

JP-A 345690/1992 discloses succinimide compounds prepared from apolyalkylene-polyamine mixture that comprises both a cyclicpolyalkylene-polyamine and an acyclic polyalkylene-polyamine. They haveno negative influence on fluoroelastomer seals, but are almostineffective for detergency at high temperatures.

JP-A 168492/1988 discloses reaction products like in JP-B 43631/1971,for which, however, used is glycolic acid as the reactant and not aboron-containing compound. As in the prior-art references, however, thereaction products are also unsatisfactory in point of their stability athigh temperatures.

Other various proposals have been made in, for example, JP-A 69758/1986,276896/1990 and 353598/1992, but could not still solve the problemsnoted above.

Given that situation, most desired in the industrial field of the artare lubricant additives and lubricants having good high-temperaturestability and good high-temperature detergency.

The invention is to solve the above-mentioned drawbacks of the prior-arttechniques, and to provide novel compounds having good high-temperaturestability and good high-temperature detergency and therefore useful forashless detergent dispersants having the ability to disperse fineparticles; additives for lubricant and fuel oil that comprise the novelcompound as the essential ingredient; and lubricants and fuel oilcompositions that contain the additive.

DISCLOSURE OF THE INVENTION

We, the present inventors have found that borosuccinimide compoundsobtained from polyalkylene-polyamines having a specific chemicalstructure are unexpectedly effective for enhancing the ability ofdetergents as high temperatures, and have further found that a mixtureof the borosuccinimide compound of the type and a specific, substitutedhydroxy-aromatic carboxylate derivative is further effective for thatpurpose. In addition, we have also found that succinimide compoundshaving a specific chemical structure and succinimide compounds obtainedthrough specific chemical reaction or physicochemical treatment of suchspecific compounds can effectively attain the object of the invention.On the basis of these findings, we have completed the present invention.Accordingly, the invention is summarized as follows:

[1] A borosuccinimide compound obtained through reaction of (a) asuccinic acid or its anhydride substituted with an alkyl or alkenylgroup having a number-average molecular weight of from 200 to 5,000, (b)a polyalkylene-polyamine of which at least 5 mol % has a terminal cyclicstructure, and (c) a boron compound.

[2] The borosuccinimide compound of above [1], for which the terminalcyclic structure of the cyclic structure-terminatedpolyalkylene-polyamine is represented by the following structuralformula (1):

wherein p and q each indicate an integer of from 2 to 4.

[3] The borosuccinimide compound of above [1] or [2], for which thecyclic structure-terminated polyalkylene-polyamine accounts for from 5to 95 mol % of all the polyalkylene-polyamine.

[4] The borosuccinimide compound of any of above [1] to [3], for whichthe cyclic structure-terminated polyalkylene-polyamine accounts for from10 to 90 mol % of all the polyalkylene-polyamine.

[5] The succinimide compound of any of above [1] to [4], for which thecyclic structure-terminated polyalkylene-polyamine is anaminoalkylpiperazine.

[6] The borosuccinimide compound of any of above [1] to [5], which has aboron content of from 0.05 to 5% by weight.

[7] A mixture of (A) the borosuccinimide compound of any of above [1] to[6], and (B) at least one compound selected from substitutedhydroxy-aromatic carboxylate derivatives of the following generalformula (2):

wherein R¹ and R² each represent an organic group having at least 6carbon atoms, and they may be the same or different; a, b, c, d and eeach are an integer satisfying 1≦a≦3, 1≦b≦3, 0≦c≦3, 1≦d≦3, 1≦e≦3,3≦(a+b+e)≦6, and 1≦(c+d)≦5; plural R¹'s and R²'s, if any, may be thesame or different,and the following general formula (3):

wherein R³, R⁴ and R⁵ each represent an organic group having at least 6carbon atoms, and they may be the same or different; f, g, h, i, j, kand m each are an integer satisfying 0≦f≦3, 0≦g≦3, 1≦(f+g)≦3, 0≦h≦4, 0≦i≦3, 1≦(h+i)≦6, 0≦j≦3, 1≦k≦3, 1≦m≦3, 0≦(f+h)≦4, 1≦(g+i+m)≦4, and1≦(j+k)≦5; and plural R³'s, R⁴'s and R⁵'s, if any, may be the same ordifferent.

[8] A lubricant additive containing the borosuccinimide compound of anyof above [1] to [6], or containing the borosuccinimidecompound-containing mixture of claim 7.

[9] A fuel oil additive containing the borosuccinimide compound of anyof above [1] to [6], or containing the borosuccinimidecompound-containing mixture of claim 7.

[10] A lubricant composition containing the lubricant additive of above[8].

[11] A fuel oil composition containing the fuel oil additive of above[9].

[12] A succinimide compound of the following general formula (I):

wherein R¹ represents an alkyl or alkenyl group having a molecularweight of from 200 to 5,000; X represents a monovalent residue derivedfrom a polyalkylene-polyamine optionally having a cyclic structure, byremoving one terminal amino group from the polyalkylene-polyamine, andthe other terminal is a group of the following general formula (II):

in which R² and R³ each independently represent a hydrogen atom or ahydrocarbon group, but R² and R³ are not hydrogen atoms at the sametime.

[13] The succinimide compound of above [12], wherein at least one of R²and R³ in formula (II) is a linear or branched alkyl group having from 1to 16 carbon atoms, or a phenyl-substituted alkyl group with the phenylgroup being optionally substituted with alkyl group(s) of the followinggeneral formula (III):

in which R⁴ represents a linear or branched alkylene group having from 1to 16 carbon atoms; R⁵ represents a linear or branched alkyl grouphaving from 1 to 16 carbon atoms; and a indicates an integer of from 0to 3,or a phenyl group optionally substituted with alkyl group(s) of thefollowing general formula (IV):

in which R⁶ represents a linear or branched alkyl group having from 1 to16 carbon atoms; and b indicates an integer of from 0 to 3.

[14] A succinimide compound obtained through (C) alkylation of areaction product of (A) a succinic acid or its anhydride substitutedwith an alkyl or alkenyl group having a molecular weight of from 200 to5,000, and (B) a polyalkylene-polyamine optionally having a cyclicstructure.

[15] The succinimide compound of above [14], for which the alkylatingagent for alkylation is a compound of the following general formula (V):R⁷—Y  (V)wherein R⁷ represents a hydrocarbon group; and Y represents a halogenatom or a sulfonic acid group.

[16] The succinimide compound of above [15], for which the hydrocarbongroup R⁷ in formula (V) is a linear or branched alkyl group having from1 to 16 carbon atoms, or a phenyl-substituted alkyl group with thephenyl group being optionally substituted with alkyl group(s) of thefollowing general formula (VI):

in which R⁸ represents a linear or branched alkylene group having from 1to 16 carbon atoms; R⁹ represents a linear or branched alkyl grouphaving from 1 to 16 carbon atoms; and c indicates an integer of from 0to 3,or a phenyl group optionally substituted with alkyl group(s) of thefollowing general formula (VII):

in which R¹⁰ represents a linear or branched alkyl group having from 1to 16 carbon atoms; and d indicates an integer of from 0 to 3.

[17] The succinimide compound of above [14], for which the alkylatingagent for alkylation is a compound of the following general formula(VIII):R¹¹ —CHO  (VIII)in which R¹¹ represents a hydrocarbon group, and the alkylationcomprises reaction with the alkylating agent followed by hydrogenation.

[18] The succinimide compound of above [16], for which the hydrocarbongroup R¹¹ in formula (VIII) is a linear or branched alkyl group havingfrom 1 to 16 carbon atoms, or a phenyl-substituted alkyl group with thephenyl group being optionally substituted with alkyl group(s) of thefollowing general formula (IX):

in which R¹² represents a linear or branched alkylene group having from1 to 16 carbon atoms; R¹³ represents a linear or branched alkyl grouphaving from 1 to 16 carbon atoms; and e indicates an integer of from 0to 3,or a phenyl group optionally substituted with alkyl group(s) of thefollowing general formula (X):

in which R¹⁴ represents a linear or branched alkyl group having from 1to 16 carbon atoms; and f indicates an integer of from 0 to 3.

[19] A succinimide compound obtained through reaction of (A) a succinicacid or its anhydride substituted with an alkyl or alkenyl group havinga molecular weight of from 200 to 5,000, with (D) ahydrocarbon-substituted polyalkylene-polyamine of the following generalformula (XI):H₂N—X  (XI)in which X represents a monovalent residue derived from apolyalkylene-polyamine optionally having a cyclic structure, by removingone terminal amino group from the polyalkylene-polyamine, and the otherterminal is a group of the following general formula (XII):

in which R¹⁵ and R¹⁶ each independently represent a hydrogen atom or ahydrocarbon group, but R¹⁵ and R¹⁶ are not hydrogen atoms at the sametime.

[20] The succinimide compound of above [18], wherein at least one of R¹⁵and R¹⁶ in formula (XII) is a linear or branched alkyl group having from1 to 16 carbon atoms, or a phenyl-substituted alkyl group with thephenyl group being optionally substituted with alkyl group(s) of thefollowing general formula (XIII):

in which R¹⁷ represents a linear or branched alkylene group having from1 to 16 carbon atoms; R¹⁸ represents a linear or branched alkyl grouphaving from 1 to 16 carbon atoms; and g indicates an integer of from 0to 3,or a phenyl group optionally substituted with alkyl group(s) of thefollowing general formula (XIV):

in which R¹⁹ represents a linear or branched alkyl group having from 1to 16 carbon atoms; and h indicates an integer of from 0 to 3.

[21] A succinimide compound containing at least 5% by weight of thesuccinimide compound of any of above [12] to [20].

[22] A succinimide compound obtained through <1> hydrogenation and/or<2> contact treatment with an adsorbent of the succinimide compound ofany of above [12] to [21].

[23] A succinimide compound obtained through reaction of the succinimidecompound of any of above [12] to [22] with a boron compound.

[24] A lubricant additive comprising, as the essential ingredient, thesuccinimide compound of any of above [12] to [23].

[25] A fuel oil additive comprising, as the essential ingredient, thesuccinimide compound of any of above [12] to [23].

[26] A lubricant composition containing the lubricant additive of above[24].

[27] A fuel oil composition containing the fuel oil additive of above[25].

BEST MODES OF CARRYING OUT THE INVENTION

Embodiments of the invention are described below.

The invention provides novel borosuccinimide compounds, and a mixturecontaining such a borosuccinimide compound and a specific, substitutedhydroxy-aromatic carboxylate derivative. The invention also providessuccinimide compounds having a specific chemical structure, andsuccinimide compounds obtained through specific chemical reaction orphysicochemical treatment of such specific compounds. Those succinimidecompounds, substituted hydroxy-aromatic carboxylate derivatives andtheir use in lubricant additives are described in detail in due orderhereinunder.

1. Borosuccinimide Compounds:

As so mentioned hereinabove, the borosuccinimide compounds of theinvention are obtained through reaction of (a) a succinic acid or itsanhydride substituted with an alkyl or alkenyl group having anumber-average molecular weight of from 200 to 5,000, (b) apolyalkylene-polyamine of which at least 5 mol % has a terminal cyclicstructure, and (c) a boron compound.

The starting materials (a), (b) and (c), and methods of their productionare described below.

Starting Material (a)

The starting material (a) to be used in the invention is a succinic acidor its anhydride substituted with an alkyl or alkenyl group.

The alkyl or alkenyl group has a number-average molecular weight(hereinafter referred to as a molecular weight or abbreviated as Mn)falling between 200 and 5,000, preferably between 500 and 2,000. If themolecular weight of the alkyl or alkenyl group is smaller than 200, thesuccinimide compounds could not well dissolve in lubricant base oil; butif larger than 5,000, the succinimide compounds will be too viscous andwill be difficult to handle.

For the alkyl or alkenyl group having the defined molecular weight,generally used are polymers or copolymers of monoolefins or diolefinshaving from 2 to 16 carbon atoms, or their hydrides. Examples of themonoolefins are ethylene, propylene, butene, butadiene, decene,dodecene, and hexadecene. Of those monoolefins, especially preferred foruse herein is butene as effective for enhancing high-temperaturedetergency and as easily available. Therefore preferred for use hereinare a polybutenyl group derived from its polymer, and a hydropolybutenylgroup, a type of an alkyl group derived from the polymer hydride.

The starting material (a), succinic acid or its anhydride substitutedwith such an alkyl or alkenyl group may be prepared by reacting apolybutene or the like of which the molecular weight falls within thedefined range of the molecular weight of the alkyl or alkenyl group asabove, with maleic anhydride or the like in a known manner.

Starting Material (b)

The starting material (b) for use in the invention is apolyalkylene-polyamine of which at least 5 mol % has a terminal cyclicstructure. Specifically, all the polyalkylene-polyamine for the startingmaterial (b) may have a terminal cyclic structure, or the startingmaterial (b) may be a mixture of a polyalkylene-polyamine having aterminal cyclic structure and a polyalkylene-polyamine not having aterminal cyclic structure. However, if the ratio of thepolyalkylene-polyamine having a terminal cyclic structure is smallerthan 5 mol % of the starting material (b), the object of the inventionto attain good high-temperature detergency could not be ensured. Theratio of at least 10 mol %, even at least 20 mol % is more preferred forthe intended object of good high-temperature detergency. In theinvention, however, the uppermost limit of the ration of thepolyalkylene-polyamine having a terminal cyclic structure in thestarting material (b) is preferably at most 95 mol %, more preferably atmost 90 mol %. If the ratio is higher than 95 mol %, the borosuccinimidecompounds to be produced will be too viscous and their productivity willlower. If so, in addition, the solubility of the products in lubricantbase oil will be low. Therefore, the ratio of the polyalkylene-polyaminehaving a terminal cyclic structure preferably falls between 5 and 95 mol%, more preferably between 10 and 90 mol %.

The terminal cyclic structure of the cyclic structure-terminatedpolyalkylene-polyamine is preferably represented by formula (1)mentioned above. In formula (1), p and q each indicate an integer offrom 2 to 4. Preferably, p and q are both 2, indicating a piperazinylgroup for the cyclic structure. Typical examples of thepolyalkylene-polyamine having such a terminal cyclic structure arepiperazinyl structure-terminated aminoalkylpiperazines, such asaminoethylpiperazine, aminopropylpiperazine, aminobutylpiperazine,amino(diethylenediamino)piperazine, amino(dipropyldiamino)piperazine. Ofthose, especially preferred is aminoethylpiperazine as easily available.

On the other hand, the polyalkylene-polyamine not having a terminalcyclic structure includes acyclic polyalkylene-polyamines not having acyclic structure, and polyalkylene-polyamines having a cyclic structurenot at their terminals.

Typical examples of the acyclic polyalkylene-polyamine arepolyethylene-polyamines such as ethylenediamine, diethylenetriamine,triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine; andpropylenediamine, dibutylenetriamine, and tributylenetriamine. Typicalexamples of the polyalkylene-polyamine having a cyclic structure not atits terminals are di(aminoalkyl)piperazines such asdi(aminoethyl)piperazine.

Of those polyalkylene-polyamines optionally having a cyclic structure,especially preferred are mixtures with a polyethylene-polyamine such astriethylenetetramine, tetraethylenepentamine or pentaethylenehexamine,as effective for enhancing high-temperature detergency and as easilyavailable.

Starting Material (c)

The starting material (c) for use in the invention is a boron compound.The boron compound includes, for example, boric acid, boric anhydride,borates, boron oxide and boron halides. Of those, especially preferredis boric acid.

Production of Borosuccinimide Compounds

The borosuccinimide compounds of the invention are reaction products tobe obtained through reaction of the starting materials (a), (b) and (c).

The method of reacting them is not specifically defined, and may be anyknown one. For example, they may be reacted in the manner mentionedbelow to obtain the intended products.

The material (a) is first reacted with the material (b), and theresulting product is then reacted with the material (c) For the blendratio of the materials (a) and (b) in their reaction, (a):(b) preferablyfalls between 0.1:1 and 10:1 by mol, more preferably between 0.5:1 and2:1 by mol. The reaction temperature of the materials (a) and (b)preferably falls between 80° C. and 250° C., more preferably between100° C. and 200° C. In their reaction, optionally used is a solvent, forexample, an organic solvent such as hydrocarbon oil, for handling thematerials with ease and for controlling the reaction.

Next, the reaction product of the materials (a) and (b) obtained in themanner as above is then reacted with the material (c). The blend ratioof the material (c), boron compound preferably falls between 1:0.05 and1:10, more preferably between 1:0.5 and 1:5 by mol, to thepolyalkylene-polyamine. The reaction temperature preferably fallsbetween 50° C. and 250° C., more preferably between 100° C. and 200° C.

Like in the reaction of the materials (a) and (b), optionally used is asolvent, for example, an organic solvent such as hydrocarbon oil, alsoin the reaction with the material (c) for handling the reactants withease and for controlling the reaction.

The reaction finally gives a product, borosuccinimide compound. Theboron content of the reaction product preferably falls between 0.05 and5% by weight, more preferably between 0.1 and 4% by weight, indicatingthe boron (atom) content of the reaction product, borosuccinimidecompound. This is an important factor in the invention. Specifically,when the borosuccinimide compound of the invention contains at least aspecific amount of boron in the molecule and when it satisfies thespecific polyalkylene-polyamine composition as above, the inventionattains the unexpected effect as above. In other words, if the boroncontent of the borosuccinimide compound is smaller than 0.05% by weight,the invention could not attain the object of high-temperaturedetergency. On the other hand, even if the boron content of the compoundis larger than 5% by weight, the intended high-temperature detergencycould not be enhanced any more, and such a high boron content of thecompound will be of little use in practice.

As so mentioned hereinabove, the borosuccinimide compound of theinvention is obtained by reacting the materials (a) and (b) followed byfurther reacting the resulting product with the material (c), but theorder of reacting them may be changed. For example, the material (a) isfirst reacted with the material (c), and the reaction product is thenreacted with the material (b). Also in this case, the intendedborosuccinimide compound is well obtained.

2. Substituted Hydroxy-Aromatic Carboxylate Ester Derivatives:

In the second aspect of the invention, the component (A),borosuccinimide compound is used along with a component (B), asubstituted hydroxy-aromatic carboxylate derivative.

The component (B) is at least one compound selected from substitutedhydroxy-aromatic carboxylate derivatives of formulae (2) and (3)mentioned above.

In formulae (2) and (3), R¹, R², R³, R⁴ and R⁵ each represent an organicgroup having at least 6 carbon atoms. The organic group having at least6 carbon atoms is preferably a hydrocarbon group having from 6 to 100,more preferably from 8 to 20 carbon atoms. The hydrocarbon groupincludes, for example, an alkyl group, an alkenyl group, a cycloalkylgroup, a cycloalkenyl group, and an aralkyl group, which may havenon-hydrocarbon substituent(s) and may have hetero atom(s) in the chainor cyclic structure. Concretely, it includes hydrocarbon groups such ashexyl, octyl, nonyl, decyl, dodecyl, hexadecyl and triacontyl groups;and groups derived from olefin polymers such as polyethylene,polypropylene and polybutene. In case where substituted hydroxy-aromaticcarboxylate derivatives of low viscosity are desired, it is preferablethat R¹, R², R³, R⁴ and R⁵ therein are substantially linear hydrocarbongroups. R¹ and R² may be the same or different; and R³, R⁴ and R⁵ mayalso be the same or different.

In formula (2), a, b, c, d and e each are an integer satisfying 1≦a≦3,1≦b≦3, 0≦c≦3, 1≦d≦3, 1≦e≦3, 3≦(a+b+e)≦6, and 1≦(c+d)≦5. When b is 2 or3, plural R¹'s may be the same or different. When d is 2 or 3, pluralR²'s may be the same or different.

In formula (3), f, g, h, i, j, k and m each are an integer satisfying0≦f≦3, 0≦g≦3, 1≦(f+g)≦3, 0≦h≦4, 0≦i≦3, 1≦(h+i)≦6, 0≦j≦3, 1≦k≦3, 1≦m≦3,0≦(f+h)≦4, 1≦(g+i+m)≦4, and 1≦(j+k)≦5. When h is 2, 3 or 4, plural R³'smay be the same or different; when i is 2 or 3, plural R⁴'s may be thesame or different; and when k is 2 or 3, plural R⁵'s may be the same ordifferent.

Examples of the substituted hydroxy-aromatic carboxylate derivatives offormula (2) are hexylphenyl (hexylhydroxybenzoate), dodecylphenyl(hexylhydroxybenzoate), octylphenyl (octylhydroxybenzoate), nonylphenyl(nonylhydroxybenzoate), hexadecylphenyl (nonylhydroxybenzoate),nonylphenyl (dodecylhydroxybenzoate), dodecylphenyl(dodecylhydroxybenzoate), hexadecylphenyl (dodecylhydroxybenzoate),hexylphenyl (hexadecylhydroxybenzoate), dodecylphenyl(hexadecylhydroxybenzoate), hexadecylphenyl (hexadecylhydroxybenzoate),eicosylphenyl (eicosylhydroxybenzoate), mixed C11-15 alkylphenyl (mixedC11-15 alkylhydroxybenzoates), dodecylphenyl (long-chainalkylhydroxybenzoates, in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400),long-chain alkylphenyl (in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400)(long-chain alkylhydroxybenzoates, in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400), hexylhydroxyphenyl (hexylhydroxybenzoate), octylhydroxyphenyl(octylhydroxybenzoate), nonylhydroxyphenyl (dodecylhydroxybenzoate),dodecylhydroxyphenyl (dodecylhydroxybenzoate), dodecylhydroxyphenyl(hexadecylhydroxybenzoate), hexadecylhydroxyphenyl(hexadecylhydroxybenzoate), eicosylhydroxyphenyl(eicosylhydroxybenzoate), mixed C11-15 alkylhydroxyphenyl (mixed C11-15alkylhydroxybenzoates), dodecylhydroxyphenyl (long-chainalkylhydroxybenzoates, in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400),long-chain alkylhydroxyphenyl (in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400) (long-chain alkylhydroxybenzoates, in which the long-chain alkylis, for example, derived from polydecenes having at least 30 carbonatoms or from polybutenes having a number-average molecular weight of atleast 400), hexylphenyl (hexyldidroxybenzoate), nonylphenyl(nonyldihydroxybenzoate), dodecylphenyl (nonyldihydroxybenzoate),nonylphenyl (dodecyldihydroxybenzoate), dodecylphenyl(dodecyldihydroxybenzoate), hexadecylphenyl(hexadecyldihydroxybenzoate), hexadecylphenyl(eicosyldihydroxybenzoate), eicosylphenyl (eicosyldihydroxybenzoate),mixed C11-15 alkylphenyl (mixed C11-15 alkyldihydroxybenzoates),dodecylphenyl (long-chain alkyldihydroxybenzoates, in which thelong-chain alkyl is, for example, derived from polydecenes having atleast 30 carbon atoms or from polybutenes having a number-averagemolecular weight of at least 400), long-chain alkylphenyl (in which thelong-chain alkyl is, for example, derived from polydecenes having atleast 30 carbon atoms or from polybutenes having a number-averagemolecular weight of at least 400) (long-chain alkyldihydroxybenzoates,in which the long-chain alkyl is, for example, derived from polydeceneshaving at least 30 carbon atoms or from polybutenes having anumber-average molecular weight of at least 400), hexylhydroxyphenyl(hexyldihydroxybenzoate), nonylhydroxyphenyl (nonyldihydroxybenzoate),dodecylhydroxyphenyl (nonyldihydroxybenzoate), nonylhydroxyphenyl(dodecyldihydroxybenzoate), dodecylhydroxyphenyl(dodecyldihydroxybenzoate), hexadecylhydroxyphenyl(hexadecyldihydroxybenzoate), hexadecylhydroxyphenyl(eicosyldihydroxybenzoate), eicosylhydroxyphenyl(eicosyldihydroxybenzoate), mixed C11-15 alkylhydroxyphenyl (mixedC11-15 alkyldihydroxybenzoates), dodecylhydroxyphenyl (long-chainalkyldihydroxybenzoates, in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400),long-chain alkylhydroxyphenyl (in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400) (long-chain alkyldihydroxybenzoates, in which the long-chain alkylis, for example, derived from polydecenes having at least 30 carbonatoms or from polybutenes having a number-average molecular weight of atleast 400).

Examples of the substituted hydroxy-aromatic carboxylate derivatives offormula (3) are hexylphenyl (hexylhydroxynaphthoate), hexadecylphenyl(hexylhydroxynaphthoate), nonylphenyl (nonylhydroxynaphthoate),dodecylphenyl (dodecylhydroxynaphthoate), hexadecylphenyl(hexadecylhydroxynaphthoate), eicosylphenyl (dodecylhydroxynaphthoate),eicosylphenyl (eicosylhydroxynaphthoate), mixed C11-15 alkylphenyl(mixed C11-15 alkylhydroxynaphthoates), dodecylphenyl (long-chainalkylhydroxynaphthoates, in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400),long-chain alkylphenyl (in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400)(long-chain alkylhydroxynaphthoates, in which the long-chain alkyl is,for example, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400), dodecylhydroxyphenyl (hexylhydroxynaphthoate),dodecylhydroxyphenyl (octylhydroxynaphthoate), dodecylhydroxyphenyl(dodecylhydroxynaphthoate), hexadecylhydroxyphenyl(dodecylhydroxynaphthoate), hexadecylhydroxyphenyl(hexadecylhydroxynaphthoate), eicosylhydroxyphenyl(hexadecylhydroxynaphthoate), mixed C11-15 alkylhydroxyphenyl (mixedC11-15 alkylhydroxynaphthoates), dodecylhydroxyphenyl (long-chainalkylhydroxynaphthoates, in which the long-chain alkyl is, for example,derived from polydecenes having at least 30 carbon atoms or frompolybutenes having a number-average molecular weight of at least 400),long-chain alkylhydroxyphenyl (in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400) (long-chain alkylhydroxynaphthoates, in which the long-chain alkylis, for example, derived from polydecenes having at least 30 carbonatoms or from polybutenes having a number-average molecular weight of atleast 400), hexylphenyl (hexyldihydroxynaphthoate), hexadecylphenyl(hexyldihydroxynaphthoate), nonylphenyl (nonyldihydroxynaphthoate),dodecylphenyl (dodecyidihydroxynaphthoate), eicosylphenyl(dodecyldihydroxynaphthoate), hexadecylphenyl(hexadecyldihydroxynaphthoate), eicosylphenyl(eicosyldihydroxynaphthoate), mixed C11-15 alkylphenyl (mixed C11-15alkyldihydroxynaphthoates), dodecylphenyl (long-chainalkyldihydroxynaphthoates, in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400), long-chain alkylphenyl (in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400) (long-chain alkyldihydroxynaphthoates, in which the long-chainalkyl is, for example, derived from polydecenes having at least 30carbon atoms or from polybutenes having a number-average molecularweight of at least 400), dodecylhydroxyphenyl(hexyldihydroxynaphthoate), dodecylhydroxyphenyl(octyldihydroxynaphthoate), dodecylhydroxyphenyl(dodecyldihydroxynaphthoate), hexadecylhydroxyphenyl(dodecyldihydroxynaphthoate), hexadecylhydroxyphenyl(hexadecyldihydroxynaphthoate), eicosylhydroxyphenyl(hexadecyldihydroxynaphthoate), mixed C11-15 alkylhydroxyphenyl (mixedC11-15 alkyldihydroxynaphthoates), dodecylhydroxyphenyl (long-chainalkyldihydroxynaphthoates, in which the long-chain alkyl is, forexample, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400) long-chain alkylhydroxyphenyl (in which the long-chain alkyl is,for example, derived from polydecenes having at least 30 carbon atoms orfrom polybutenes having a number-average molecular weight of at least400) (long-chain alkyldihydroxynaphthoates, in which the long-chainalkyl is, for example, derived from polydecenes having at least 30carbon atoms or from polybutenes having a number-average molecularweight of at least 400).

Of the substituted hydroxy-aromatic carboxylate derivatives, preferredare those of the following general formula (4):

wherein R¹, R², b, d and e have the same meanings as above; and the sumof b and e falls between 2 and 5, and those of the following generalformula (4′):

wherein R³, R⁴, R⁵, h, k and m have the same meanings as above; nindicates 0, 1 or 2; the sum of h and n falls between 1 and 6; and thesum of m and n falls between 1 and 3.

The component (B) in the invention may be one or more of the substitutedhydroxy-aromatic carboxylate derivatives of formula (2); or may be oneor more of those of formula (3); or may be a combination of one or moreof those of formula (2) and one or more of those of formula (3).

In the borosuccinimide compound-containing mixture of the invention, theblend ratio of the component (A), borosuccinimide compound to thecomponent (B), at least one compound selected from substitutedhydroxy-aromatic carboxylate derivatives of formulae (2) and (3)preferably falls between 1:99 and 99:1, more preferably between 10:90and 90:10 by weight.

3. Use:

The borosuccinimide compounds of the invention are effectively used fordetergent dispersants. The detergent dispersant comprising the compoundmay be added to hydrocarbon oil or synthetic oil in a ratio fallingbetween 0.1 and 80% by weight to prepare a lubricant composition. Theblend ratio preferably falls between 0.5 and 30% by weight.

The detergent dispersant may also be added to hydrocarbon oil serving asfuel oil. Its blend ratio preferably falls between 0.001 and 1% byweight.

The hydrocarbon oil may be any fraction, including, for example, fueloil such as gasoline, kerosene, gas oil; and lubricant oil (e.g.,paraffinic mineral oil, naphthenic mineral oil, aromatic mineral oil),and it may be purified in any method of solvent purification,hydrogenation purification or hydrogenation cracking. The synthetic oilincludes, for example, polyphenyl ethers, alkylbenzenes,alkylnaphthalenes, ester oils, glycolic or polyolefinic synthetic oils.The lubricant oil fraction preferably has a kinematic viscosity at 100°C. falling between 1 and 50 mm²/sec, more preferably between 3 and 20mm²/sec.

The mixtures prepared by adding the succinimide compound to lubricantoil fractions such as hydrocarbon oil, synthetic oil or their mixturescan be used for lubricant oil compositions for internal-combustionengines (e.g., lubricant oil compositions for diesel engines), gear oil,bearing oil, transmission oil, shock absorber oil and other industriallubricant oils.

In the invention, any ordinary additives for lubricant oil, such asantioxidant, anti-wear additive, viscosity index improver and pour pointdepressant may be used, not interfering with the effect of thesuccinimide compounds of the invention.

The mixture prepared by adding the succinimide compound to hydrocarbonfuel oil serves as a detergent for preventing deposition of impuritiesin internal-combustion engine carburetors and for removing the depositstherein.

The succinimide compounds having a specific structure of the inventionare represented by formula (I) mentioned above.

In formula (I), R¹ represents an alkyl or alkenyl group having anumber-average molecular weight (Mn, hereinafter referred to as“molecular weight”) of from 200 to 5,000, preferably from 500 to 2,000.

If the molecular weight of the alkyl or alkenyl group is smaller than200, the succinimide compounds could not well dissolve in lubricant baseoil; but if larger than 5,000, the succinimide compounds will be tooviscous and will be difficult to handle.

For the alkyl or alkenyl group having the defined molecular weight,generally used are polymers or copolymers of monoolefins or diolefinshaving from 2 to 16 carbon atoms, or their hydrides. Examples of themonoolefins are ethylene, propylene, butene, butadiene, decene,dodecene, and hexadecene. Of those monoolefins, especially preferred foruse herein is butene as effective for enhancing high-temperaturedetergency and as easily available. Therefore preferred for use hereinare a polybutenyl group derived from its polymer, and a hydropolybutenylgroup, a type of an alkyl group derived from the polymer hydride.

In the invention, X in formula (I) represents a monovalent residuederived from a polyalkylene-polyamine optionally having a cyclicstructure, by removing one terminal amino group from thepolyalkylene-polyamine, and the other terminal, or that is, the terminalof the compound of formula (I) is represented by formula (II) mentionedabove. This means that the compound of formula (I) is terminated with asecondary or tertiary amine, and we, the present inventors have foundthat the succinimide compounds having such a specific chemical structureare effective for significantly enhancing the properties of detergentssuch as high-temperature detergency thereof.

The succinimide compounds terminated with a secondary or tertiary amineare also significantly effective even though they contain any othersuccinimides not having such a specific chemical structure. Preferably,in the invention, the secondary or tertiary amine-terminatedsuccinimides account for at least 5% by weight, more preferably at least10% by weight, even more preferably at least 30% by weight of allsuccinimide compounds.

X in formula (I) is described in more detail hereinunder.

The polyalkylene-polyamine optionally having a cyclic structure meansthat it may be any of linear or branched, or that is, acyclicpolyalkylene-polyamines, cyclic polyalkylene-polyamines, and theirmixtures.

Typical examples of the acyclic polyalkylene-polyamine areethylenediamine, propylenediamine, diethylenetriamine,triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine,dibutylenetriamine, and tributylenetriamine. Typical examples of thecyclic polyalkylene-polyamine are piperazinyl structure-havingaminoalkylpiperazines and di(aminoalkyl)piperazines such asaminoethylpiperazine, aminopropylpiperazine, aminobutylpiperazine,amino(diethylenediamino)piperazine, amino(dipropyldiamino)piperazine.

Of those, especially preferred are triethylenetetramine,tetraethylenepentamine, pentaethylenehexamine, andaminoalkylpiperazines, as effective for enhancing high-temperaturedetergency and as easily available.

In addition to the above-mentioned requirement, X in formula (I) in theinvention must satisfy another requirement that the other terminalstructure is represented by formula (II).

In formula (II) , R² and R³ each independently represent a hydrogen atomor a hydrocarbon group, and they may be the same or different. However,both of them must not be hydrogen atoms at the same time. In otherwords, at least any one of R² and R³ is a hydrocarbon group.

The hydrocarbon group is not specifically defined, but preferably hasfrom 1 to 50, more preferably from 1 to 30 carbon atoms. The hydrocarbongroup includes, for example, a linear or branched, saturated orunsaturated alkyl group, a cycloalkyl group, an aryl group, analkyl-substituted aryl group, and an aryl-substituted alkyl group.

In preferred embodiments of the invention, the hydrocarbon group for R²or R³ in formula (II) is an alkyl group, or a phenyl-substituted alkylgroup with the phenyl group being optionally substituted with alkylgroup(s), or a phenyl group optionally substituted with alkyl group(s).More preferably, it is a linear or branched alkyl group having from 1 to16 carbon atoms, or a phenyl-substituted alkyl group with the phenylgroup being optionally substituted with alkyl group(s) of formula (III),or a phenyl group optionally substituted with alkyl group(s) of formula(IV).

Examples of the linear or branched alkyl group having from 1 to 16carbon atoms are a methyl group, an ethyl group, an n-propyl group, anisopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group,all types of amyl groups, all types of hexyl groups, all types of octylgroups, a decyl group, a dodecyl group, and a hexadecyl group. Of those,especially preferred are alkyl groups having from 2 to 12 carbon atoms.

R⁴ in formula (III) that represents a phenyl-substituted alkyl groupwith the phenyl group being optionally substituted with alkyl group(s)indicates a linear or branched alkylene group having from 1 to 16 carbonatoms; and R⁵ therein indicates a linear or branched alkyl group havingfrom 1 to 16 carbon atoms.

Examples of the linear or branched alkylene group having from 1 to 16carbon atoms for R⁴ are a methylene group, an ethylene group, ann-propylene group, an isopropylene group, an n-butylene group, anisobutylene group, a sec-butylene group, all types of amylene groups,all types of hexylene groups, all types of octylene groups, a decylenegroup, a dodecylene group, and a hexadecylene group. Of those,especially preferred are alkylene groups having from 2 to 12 carbonatoms.

For R⁵ indicating a linear or branched alkyl group having from 1 to 16carbon atoms for R⁵, referred to are the examples of the linear orbranched alkyl group having from 1 to 16 carbon atoms mentionedhereinabove.

In formula (III), a indicates an integer of from 0 to 3, but ispreferably 1.

In formula (IV) representing a phenyl group optionally substituted withalkyl group(s), R⁶ indicates a linear or branched alkyl group havingfrom 1 to 16 carbon atoms, for which also referred to are the examplesof the linear or branched alkyl group having from 1 to 16 carbon atomsmentioned hereinabove. In formula (IV), b indicates an integer of from 0to 3, but is preferably 1.

Accordingly, preferred examples of X in formula (I) are monovalentresidues derived from polyalkylene-polyamines mentioned below, byremoving the terminal amino group from them.

The polyalkylene-polyamines are 1-alkylpolyalkylene-polyamines,including, for example, 1-ethylethylenediamine, 1-propylethylenediamine,1-butylethylenediamine, 1-propyldiethylenetriamine,1-propyltriethylenetetramine, 1-propyltetraethylenepentamine,1-propylpentaethylenehexamine, 1-propyldibutylenetriamine,1-propyltributylenetetramine, 1-butyldiethylenetriamine,1-butyltriethylenetetramine, 1-butyltetraethylenepentamine,1-butylpentaethylenehexamine, 1-butyldibutylenetriamine,1-butyltributylenetetramine.

The second succinimide compounds having a specific structure of theinvention are obtained through (C) alkylation of a reaction product of(A) a succinic acid or its anhydride substituted with an alkyl oralkenyl group having a molecular weight of from 200 to 5,000, and (B) apolyalkylene-polyamine optionally having a cyclic structure.

For these, the starting material (A), a succinic acid or its anhydridesubstituted with an alkyl or alkenyl group having a molecular weight offrom 200 to 5,000 may be prepared by introducing the specific alkyl oralkenyl group into a succinic acid or its anhydride.

The alkyl or alkenyl group may be the same as that indicated R¹ informula (I) mentioned above. Accordingly, preferred examples of thegroup are a polybutenyl group having a molecular weight of from 200 to5,000, preferably from 500 to 2,000, and a hydropolybutenyl group, atype of an alkyl group derived from the polybutenyl group throughhydrogenation.

The starting material (B), a polyalkylene-polyamine optionally having acyclic structure includes acyclic polyalkylene-polyamines, cyclicpolyalkylene-polyamines, and their mixtures. For these, referred to arethe examples of the polyalkylene-polyamine optionally having a cyclicstructure mentioned hereinabove for X in formula (I). Needless-to-say,however, the limitation on X in formula (I) indicating that its terminalis a specific hydrocarbon should not apply to thepolyalkylene-polyamines for the starting material (B).

In the invention, the reaction products of (A) and (B) is alkylated togive the succinimide compounds. (A) and (B) maybe reacted in any knownmanner. For example, the blend ratio of the materials (A) and (B) to bereacted is preferably such that (A):(B) falls between 0.1:1 and 10:1 bymol, more preferably between 0.5:1 and 2:1 by mol.

The temperature for the reaction of (A) and (B) preferably falls between80° C. and 250° C., more preferably between 100° C. and 200° C. In thereaction, optionally used is a solvent, for example, an organic solventsuch as hydrocarbon oil for handling the materials with ease and forcontrolling the reaction.

In the invention, the reaction product of (A) and (B) obtained in themanner as above is further alkylated (C) to give the succinimidecompounds.

The alkylation is not specifically defined, for which, for example,preferred are (C-1) a method of using the compound of formula (V)mentioned above for the alkylating agent; and (C-2) a method of usingthe compound of formula (VIII) mentioned above for the alkylating agent,in which the alkylation is followed by hydrogenation.

In the alkylation method (C-1), used is the alkylating agent of formula(V) in which R⁷ indicates a hydrocarbon group. Preferably, thehydrocarbon group has from 1 to 50 carbon atoms, more preferably from 1to 30 carbon atoms. For this, referred to is the hydrocarbon group of R²and R³ of formula (II) that constitutes the terminal structure offormula (I). Accordingly, preferred examples of the hydrocarbon groupfor R⁷ are an alkyl group, a phenyl-substituted alkyl group with thephenyl group being optionally substituted with alkyl group(s), and aphenyl group optionally substituted with alkyl group(s). More preferredfor the hydrocarbon group for R⁷ are a linear or branched alkyl grouphaving from 1 to 16 carbon atoms, a phenyl-substituted alkyl group withthe phenyl group being optionally substituted with alkyl group(s) offormula (VI), and a phenyl group optionally substituted with alkylgroup(s) of formula (VII). In formula (VI), R⁸, R⁹ and c have the samemeanings as R⁴, R⁵ and a, respectively, in formula (III). In formula(VII), R¹⁰ and d have the same meanings as R⁶ and b in formula (IV).

Y in formula (V) represents a halogen atom or a sulfonic acid group.Concretely, the halogen atom includes fluorine, chlorine, bromine andiodine atoms; and the sulfonic acid group includes a toluenesulfonicacid group and a methanesulfonic acid group. The alkylation of thereaction product of (A) and (B) with the alkylating agent mentionedabove may be effected under any ordinary condition. For example, in themethod (C-1), the blend ratio of the alkylating agent based on thematerial (B) in the reaction products (A) and (B) is preferably suchthat (B):(alkylating agent in C-1) falls between 1:0.1 and 1:10 by mol,more preferably between 1:0.5 and 1:5 by mol.

The reaction temperature preferably falls between 0° C. and 200° C.,more preferably between 0° C. and 150° C. Like in the reaction of (A)and (B), a solvent may be optionally used in the alkylation.

Next described is the alkylation method (C-2) of the reaction product of(A) and (B).

The alkylating agent for the alkylation (C-2) is, for example,represented by formula (VIII). For the hydrocarbon group for R¹¹,referred to is that for R⁷ in formula (V) mentioned hereinabove.Accordingly, especially preferred examples of the hydrocarbon group forR⁷ are a linear or branched alkyl group having from 1 to 16 carbonatoms, a phenyl-substituted alkyl group with the phenyl group beingoptionally substituted with alkyl group(s) of formula (IX), and a phenylgroup optionally substituted with alkyl group(s) of formula (X). Informula (IX), R¹², R¹³ and e have the same meanings as R⁴, R⁵ and a,respectively, in formula (III). In formula (X), R¹⁴ and f have the samemeanings as R⁶ and b in formula (IV).

For the reaction condition of the alkylation of the reaction product of(A) and (B) with the alkylating agent of formula (VII) in (C-2),referred to is the same as in (C-1) mentioned hereinabove.

In the alkylation (C-2), the reaction product (A) and (B) alkylated withthe alkylating agent is then hydrogenated. The condition for thehydrogenation is not specifically defined. For example, the alkylatedproduct may be hydrogenated with hydrogen being applied thereto or in ahydrogen atmosphere, in the presence of a hydrogenation catalyst.

For the hydrogenation catalyst, generally used is a metallic componentheld on a carrier. Concretely, the catalyst comprises a metalliccomponent, for example, an element of Groups 8 to 10 of the PeriodicTable such as nickel, ruthenium, palladium, platinum, rhodium oriridium, held on an inorganic oxide carrier such as diatomaceous earth,alumina, silica, alumina or activated carbon. Above all, preferred arenickel, palladium and platinum catalysts in view of their selectivity.Concretely, they include nickel/diatomaceous earth,nickel/silica-alumina, Raney nickel, palladium/carbon,palladium/silica-alumina, and platinum oxide.

The reaction temperature for the hydrogenation is not specificallydefined, but preferably falls between 0° C. and 200° C., more preferablybetween 50° C. and 150° C. If the hydrogenation temperature is lowerthan 0° C., the hydrogenation speed is low and is thereforeuneconomical; but if higher than 200° C., the product will decompose andits yield will lower.

The reaction pressure for the hydrogenation is not also specificallydefined, but preferably falls between 0 and 30 MPa (G), more preferablybetween 0.1 and 10 MPa (G).

The third succinimide compounds having a specific structure of theinvention are obtained through reaction of (A) a succinic acid or itsanhydride substituted with an alkyl or alkenyl group having a molecularweight of from 200 to 5,000, with (D) a hydrocarbon-substitutedpolyalkylene-polyamine.

For the starting material (A) for these, referred to are the same forthe material (A) mentioned hereinabove.

For the starting material (D), generally used arehydrocarbon-substituted polyalkylene-polyamines of formula (XI)mentioned above.

In formula (XI), X indicates a monovalent residue derived from apolyalkylene-polyamine optionally having a cyclic structure, by removingone terminal amino group from the polyalkylene-polyamine, and the otherterminal is a group of the following general formula (XII). The groupfor X in formula (XI) maybe the same as that for X in formula (I).Specifically, in formula (XII), R¹⁵ and R¹⁶ have the same meanings as R²and R³, respectively, in formula (II). Accordingly, especially preferredexamples of the hydrocarbon group for R¹⁵ and R¹⁶ in formula (XII) are alinear or branched alkyl group having from 1 to 16 carbon atoms, aphenyl-substituted alkyl group with the phenyl group being optionallysubstituted with alkyl group(s) of formula (XIII), and a phenyl groupoptionally substituted with alkyl group(s) of formula (XIV). In formula(XIII), R¹⁷, R¹⁸ and g have the same meanings as R⁴, R⁵ and a,respectively, in formula (III). In formula (XIV), R¹⁹ and h have thesame meanings as R⁶ and b in formula (IV).

Preferred examples of the hydrocarbon-substituted polyalkylene-polyamine(D) are 1-alkylpolyalkylene-polyamines polyamines such as1-ethylethylenediamine, 1-propylethylenediamine, 1-butylethylenediamine,1-propyldiethylenetriamine, 1-propyltriethylenetetramine,1-propyltetraethylenepentamine, 1-propylpentaethylenehexamine,1-propyldibutylenetriamine, 1-propyltributylenetetramine,1-butyldiethylenetriamine, 1-butyltriethylenetetramine,1butyltetraethylenepentamine, 1-butylpentaethylenehexamine,1-butyldibutylenetriamine, 1-butyltributylenetetramine.

One or more of these may be used herein.

The reaction of (A) and (D) in the invention is not specificallydefined, and may be effected in any ordinary manner. Regarding the blendratio of the reactants, (A):(D) preferably falls between 1:1 and 10:1 bymol, more preferably between 1:1 and 2:1 by mol.

The temperature for the reaction of (A) and (D) preferably falls between80° C. and 250° C., more preferably between 100° C. and 200° C. Like inthe other cases mentioned hereinabove, a solvent may also be used inthis reaction.

The fourth succinimide compounds having a specific structure of theinvention are obtained through <1> hydrogenation and/or <2> contacttreatment with an adsorbent of the succinimide compounds mentionedhereinabove.

In the invention, the hydrocarbon-substituted succinimides mentionedabove may be subjected to the hydrogenation <1> alone, or may besubjected to the adsorbent contact treatment <2> alone. In case wherethey are subjected to both <1> and <2>, the order of the treatments isnot defined. Thus processed, the succinimide compounds are furtherimproved to have better high-temperature detergency.

The hydrogenation <1> is effected generally in the presence of ahydrogenation catalyst.

The hydrogenation catalyst may comprise a metallic component held on acarrier. For its examples, referred to are those mentioned hereinabovefor the hydrogenation catalyst in the method (C-2) comprising alkylationfollowed by hydrogenation.

The hydrogenation temperature is not specifically defined, butpreferably falls between 0° C. and 200° C., more preferably between 20°C. and 150° C. If the hydrogenation temperature is lower than 0° C., thehydrogenation speed is low and is therefore uneconomical; but if higherthan 200° C., the product will decompose and its yield will lower.

The reaction pressure for the hydrogenation is not also specificallydefined, but preferably falls between 0 and 30 MPa (G), more preferablybetween 0.1 and 10 MPa (G).

The hydrogenation time generally falls between 30 minutes and 5 hours orso

In the other method <2> of contact with an adsorbent, the succinimidecompounds or their compositions are efficiently contacted with anadsorbent.

The adsorbent includes, for example, activated carbon, other carbons,graphite, diatomaceous earth, clay, zeolite, hydrotalcite, silica andalumina. Of those, preferred for use herein are activated carbon,diatomaceous earth, clay, silica and alumina, as their adsorptionefficiency is high. Two or more such adsorbents may be used herein.

In the contact treatment, the succinimide compounds may be optionallydiluted with a solvent for handling the compounds with ease and forincreasing the contact efficiency.

The solvent for dilution is not specifically defined. For example,employable are organic solvents such as petroleum hydrocarbons, hexane,heptane, cyclohexane, toluene and xylene.

The temperature for the contact treatment preferably falls between 0° C.and 200° C., more preferably between 20° C. and 150° C.

For the adsorbent contact treatment, concretely, from 0.1 to 10% byweight of the adsorbent is added to the succinimide compounds or theirdilutions in solvent, and stirred at a predetermined temperature.

The fifth succinimide compounds having a specific structure of theinvention are obtained through reaction of the succinimides mentionedabove with (E) a boron compound.

The boron content of the reaction products, succinimide compoundspreferably falls between 0.05 and 5% by weight, more preferably between0.1 and 4% by weight in terms of the boron atom.

The boron compound (E) includes, for example, boric acid, boricanhydride, borates, boron oxide, and boron halides.

The blend ratio of the boron compound in the reaction is preferably suchthat the molar ratio of the boron compound to the polyalkylene-polyaminefalls between 1:0.05 and 1:10, more preferably between 1:0.5 and 1:5.

The reaction temperature preferably falls between 50° C. and 250° C.,more preferably between 100° C. and 200° C.

In the reaction, optionally used is a solvent, for example, an organicsolvent such as hydrocarbon oil, for handling the succinimides with easeand for controlling the reaction.

In the description given above, the succinimides are reacted with aboron compound after they are subjected to <1> hydrogenation and/or <2>adsorbent contact treatment. In the invention, however, they may befirst reacted with a boron compound, and then subjected to <1>hydrogenation and/or <2> adsorbent contact treatment.

The succinimide compounds of the invention are effectively used fordetergent dispersants. The detergent dispersant containing the compoundmay be mixed with lubricant base oil such as hydrocarbon oil orsynthetic oil, to an amount of from 0.1 to 80% by weight to prepare alubricant oil composition. The blend ratio of the detergent dispersantpreferably falls between 0.5 and 30% by weight.

The detergent dispersant may also be added to hydrocarbon oil for fueloil. Its blend ratio preferably falls between 0.001 and 1% by weight.

The hydrocarbon oil may be any fraction, including, for example, fueloil such as gasoline, kerosene, gas oil; and lubricant oil (e.g.,paraffinic mineral oil, naphthenic mineral oil, aromatic mineral oil),and it may be purified in any method of solvent purification,hydrogenation purification or hydrogenation cracking. The synthetic oilincludes, for example, polyphenyl ethers, alkylbenzenes,alkylnaphthalenes, ester oils, glycolic or polyolefinic synthetic oils.The lubricant oil fraction preferably has a kinematic viscosity at 100°C. falling between 1 and 50 mm²/sec, more preferably between 3 and 20mm²/sec.

The mixtures prepared by adding the succinimide compound to lubricantoil fractions such as hydrocarbon oil, synthetic oil or their mixturescan be used for lubricant oil compositions for internal-combustionengines (e.g., lubricant oil compositions for diesel engines), gear oil,bearing oil, transmission oil, shock absorber oil and other industriallubricant oils.

In the invention, any ordinary additives for lubricant oil, such asantioxidant, anti-wear additive, viscosity index improver and pour pointdepressant maybe used, not interfering with the effect of thesuccinimide compounds of the invention.

The mixture prepared by adding the succinimide compound to hydrocarbonfuel oil serves as a detergent for preventing deposition of impuritiesin internal-combustion engine carburetors and for removing the depositstherein.

The invention is described more concretely with reference to thefollowing Examples, which, however, are not intended to restrict thescope of the invention.

EXAMPLE 1

550 g of polybutene (Mn: 980), 1.5 g (0.005 mol) of cetyl bromide, and59 g (0.6 mol) of maleic anhydride were put into a one-liter autoclave,purged with nitrogen, and reacted at 240° C. for 5 hours. This wascooled to 215° C., and the non-reacted maleic anhydride and cetylbromide were removed through distillation under reduced pressure. Thiswas further cooled to 140° C., and then filtered. The yield of theresulting polybutenylsuccinic anhydride was 550 g, and thesaponification value thereof was 86 mg KOH/g. 500 g of thepolybutenylsuccinic anhydride was put into a one-liter separable flaskalong with 22 g (0.17 mol) of aminoethylpiperazine (AEP), 18 g (0.17mol) of diethylenetriamine (EDTA) and 250 g of 150-neutral fractionmineral oil thereinto, and reacted in a nitrogen stream atmosphere at150° C. for 2 hours. This was heated up to 200° C., and the non-reactedAEP and EDTA and the water formed were removed through distillationunder reduced pressure. The yield of the resultingpolybutenylsuccinimide was 750 g, and the base value (measured accordingto a perchloric acid method) was 51 mg KOH/g. 150 g of thepolybutenylsuccinimide and 20 g of boric acid were put into a 500-mlseparable flask, and reacted in a nitrogen stream atmosphere at 150° C.for 4 hours. The water formed was removed through distillation underreduced pressure at 150° C., and this was cooled to 140° C. andfiltered. The yield of the product was 165 g, and the boron contentthereof was 2.1% by weight.

EXAMPLE 2

The same process as in Example 1 was repeated. In this, however, usedwere 22 g (0.17 mol) of aminoethylpiperazine (AEP) and 25 g (0.17 mol)of triethylenetetramine (TETA) in place of 22 g (0.17 mol) ofaminoethylpiperazine (AEP) and 18 g (0.17 mol) of diethylenetriamine(DETA). The yield of the product obtained herein was 165 g, and theboron content thereof was 2.1% by weight.

EXAMPLE 3

The same process as in Example 1 was repeated. In this, however, usedwere 31 g (0.24 mol) of aminoethylpiperazine (AEP) and 10 g (0.10 mol)of diethylenetriamine (DETA) in place of 22 g (0.17 mol) ofaminoethylpiperazine (AEP) and 18 g (0.17 mol) of diethylenetriamine(DETA). The yield of the product obtained herein was 160 g, and theboron content thereof was 2.1% by weight.

EXAMPLE 4

The same process as in Example 1 was repeated. In this, however, usedwere 5 g (0.04 mol) of aminoethylpiperazine (AEP) and 31 g (0.30 mol) ofdiethylenetriamine (DETA) in place of 22 g (0.17 mol) ofaminoethylpiperazine (AEP) and 18 g (0.17 mol) of diethylenetriamine(DETA). The yield of the product obtained herein was 165 g, and theboron content thereof was 2.2% by weight.

EXAMPLE 5

The same process as in Example 1 was repeated. In this, however, usedwere 14 g (0.11 mol) of aminoethylpiperazine (AEP), 11.5 g (0.11 mol) ofdiethylenetriamine (DETA) and 16 g (0.11 mol) of triethylenetetramine(TETA) in place of 22 g (0.17 mol) of aminoethylpiperazine (AEP) and 18g (0.17 mol) of diethylenetriamine (DETA). The yield of the productobtained herein was 165 g, and the boron content thereof was 2.1% byweight.

EXAMPLE 6

The same process as in Example 1 was repeated. In this, however, usedwas 44 g (0.34 mol) of aminoethylpiperazine (AEP) in place of 22 g (0.17mol) of aminoethylpiperazine (AEP) and 18 g (0.17 mol) ofdiethylenetriamine (DETA). The yield of the product obtained herein was155 g, and the boron content thereof was 2.0% by weight. Different fromthe products in Examples 1 to 5, the product obtained herein was highlyviscous and was difficult to handle.

COMPARATIVE EXAMPLE 1

The same process as in Example 1 was repeated. In this, however, usedwas 50 g (0.34 mol) of triethylenetetramine (TETA) only, in place of 22g (0.17 mol) of aminoethylpiperazine (AEP) and 18 g (0.17 mol) ofdiethylenetriamine (DETA). The yield of the product obtained herein was165 g, and the boron content thereof was 2.0% by weight.

COMPARATIVE EXAMPLE 2

Herein used was the polybutenylsuccinimide of Comparative Example 1 notas yet subjected to boronation.

COMPARATIVE EXAMPLE 3

Herein used was the polybutenylsuccinimide of Example 1 not as yetsubjected to boronation.

EXAMPLES 7 TO 12, AND COMPARATIVE EXAMPLES 4 to 6

10% by weight of the succinimide compound obtained in any of Examples 1to 6 and Comparative Examples 1 to 3 was added to 500-neutral fractionmineral oil to prepare lubricant oil compositions.

The lubricant oil compositions were tested to evaluate their properties,according to a hot tube test method mentioned below. The results aregiven in Table 1.

EXAMPLES 13 TO 18

7.5% by weight of the imide obtained in any of Examples 1 to 5, and 2.5%by weight of dodecylphenyl dodecylsalicylate were added to 500-neutralfraction mineral oil to prepare lubricant oil compositions. Thelubricant oil compositions were tested to evaluate their properties,according to the hot tube test method. The results are given in Table 1.

[Hot Tube Test Condition]

0.3 ml/hr of a sample oil to be tested was kept led into a glass tubehaving an inner diameter of 2 mm for 16 hours, along with 10 ml/min ofair thereinto, while the temperature in the glass tube was kept at 270°C. during the process. The lacquer deposited on the inner wall of theglass tube was compared with a color index. The transparent tube is 10points; and the black tube is 0 point. The weight of the lacquer wasmeasured. The higher point and the lower lacquer weight mean bettersamples.

TABLE 1 Type of Imide Hot Tube Test (270° C.) Compound Point Deposit(mg) Example 7 Example 1 8 1 or less Example 8 Example 2 8 1 or lessExample 9 Example 3 8 1 or less Example 10 Example 4 7 1 or less Example11 Example 5 8 1 or less Example 12 Example 6 8 1 or less Example 13Example 1 10 1 or less Example 14 Example 2 10 1 or less Example 15Example 3 10 1 or less Example 16 Example 4 10 1 or less Example 17Example 5 10 1 or less Example 18 Example 6 10 1 or less Comp. Example 4Comp. Example 1 2 3 Comp. Example 5 Comp. Example 2 0 32 Comp. Example 6Comp. Example 3 0 24

When the data of Examples 7 to 12 are compared with those of ComparativeExamples 1 to 3 in Table 1, the unexpected effect of the invention isobvious in that the lubricant oil compositions containing theborosuccinimide compound of the invention all gained much higher pointsand gave much less deposit in the hot tube test at 270° C. than thosecontaining the conventional succinimide compound.

When the data of Examples 13 to 18 are compared with those of Examples 7to 12 in Table 1, it is understood that the lubricant oil compositionscontaining a mixture of the borosuccinimide compound and dodecylphenyldodecylsalicylate gained much higher points and are therefore moreeffective than those containing the borosuccinimide compound only.

PRODUCTION EXAMPLE 1

1100 g of polybutene (Mw: 987), 6.4 g (0.021 mol) of cetyl bromide and115 g (1.2 mols) of maleic anhydride were put into a 2-liter autoclave,purged with nitrogen, and reacted at 240° C. for 5 hours. This wascooled to 215° C., and the non-reacted maleic anhydride and cetylbromide were removed through distillation under reduced pressure. Thiswas further cooled to 140° C., and then filtered. The yield of theresulting polybutenylsuccinic anhydride was 1100 g, and thesaponification value thereof was 80 mg KOH/g. 500 g of thepolybutenylsuccinic anhydride was put into a 2-liter separable flaskalong with 64 g (0.34 mol) of tetraethylenepentamine (TEPA) and 300 g of150-neutral fraction mineral oil thereinto, and reacted in a nitrogenstream atmosphere at 150° C. for 2 hours. This was heated up to 200° C.,and the non-reacted TEPA and the water formed were removed throughdistillation under reduced pressure. This was cooled to 140° C. andfiltered. The yield of the resulting polybutenylsuccinimide was 790 g,the base value thereof was 77 mg KOH/g, and the kinematic viscosity(100° C.) thereof was 149 mm²/sec.

PRODUCTION EXAMPLE 2

The same process as in Production Example 1 was repeated. In this,however, used was 915 g of polybutene (Mw: 800) in place of polybutene(Mw: 987). The yield of the resulting polybutenylsuccinic anhydride was940 g, and the saponification value thereof 95 mg KOH/g. Next, also inthe same manner as in Production Example 1, 500 g of thepolybutenylsuccinic anhydride was reacted with 76 g (0.40 mol) oftetraethylenepentamine (TEPA) in 300 g of 150-neutral fraction mineraloil. The yield of the resulting polybutenylsuccinimide was 810 g, thebase value thereof was 85 mg KOH/g, and the kinematic viscosity (100°C.) thereof was 109 mm²/sec.

PRODUCTION EXAMPLE 3

The same process as in Production Example 1 was repeated. In this,however, used were 890 g of polybutene (Mw: 445) in place of polybutene(Mw: 987), and 11 g (0.036 mol) of cetyl bromide and 397 g (2.1 mols) ofmaleic anhydride. The yield of the resulting polybutenylsuccinicanhydride was 990 g, and the saponification value thereof 142 mg KOH/g.Next, also in the same manner as in Production Example 1, 500 g of thepolybutenylsuccinic anhydride was reacted with 88 g (0.60 mol) oftriethylenetetramine (TETA) in 300 g of 150-neutral fraction mineraloil. The yield of the resulting polybutenylsuccinimide was 820 g, thebase value thereof was 98 mg KOH/g, and the kinematic viscosity (100°C.) thereof was 130 mm²/sec.

EXAMPLE 19

100 g of the polybutenylsuccinimide prepared in Production Example 1 wasput into a 300-ml autoclave along with 4.3 g (0.06 mol) ofn-butylaldehyde, 100 ml of n-hexane and 1 g of 5% palladium-carbon, andthe autoclave was purged with hydrogen gas. The hydrogen pressure waskept at 1 MPa (G), and these were reacted at room temperature for 2hours with stirring, then heated up to 100° C., and further reacted for6 hours. After cooled, the reaction product was taken out, and filtered.N-hexane was evaporated away, and the yield of the product was 101 g.

EXAMPLE 20

The polybutenylsuccinimide was reacted in the same manner as in Example19, for which, however, used was 6.4 g (0.06 mol) of benzaldehyde inplace of n-butylaldehyde. The yield of the product obtained herein was102 g.

EXAMPLE 21

100 g of the polybutenylsuccinimide prepared in Production Example 2,and not the polybutenylsuccinimide prepared in Production Example 1, wasreacted with 5.0 g (0.07 mol) of n-butylaldehyde in the same manner asin Example 19. The yield of the product was 102 g.

EXAMPLE 22

100 g of the polybutenylsuccinimide prepared in Production Example 3,and not the polybutenylsuccinimide prepared in Production Example 1, wasreacted with 8.6 g (0.12 mol) of n-butylaldehyde in the same manner asin Example 19. The yield of the product was 104 g.

EXAMPLE 23

20 g (0.14 mol) of triethylenetetramine (TETA), 10 g (0.14 mol) ofn-butylaldehyde and 0.7 g of 5% palladium-carbon were put into a 300-mlautoclave, and purged with hydrogen gas. The hydrogen pressure was keptat 1 MPa (G), and these were heated up to 100° C. and reacted for 6hours. After cooled, the reaction product was taken out, and filtered.The yield of the product was 28 g. 22 g (0.11 mol) of the product wasput into a 500-ml separable flask along with 175 g of the intermediatein Production Example 1, polybutenylsuccinic anhydride and 105 g of150-neutral fraction mineral oil thereinto, and these were reacted in anitrogen stream atmosphere at 150° C. for 2 hours. This was heated up to200° C., and the non-reacted matter and the water formed were removedthrough distillation under reduced pressure. This was cooled to 140° C.and filtered. The yield of the resulting polybutenylsuccinimide was 270g, the base value thereof was 61 mg KOH/g, and the kinematic viscosity(100° C.) thereof was 140 mm²/sec.

EXAMPLES 24 TO 28

60 g of the polybutenylsuccinimide obtained in any of Examples 19 to 23,and 8 g of boric acid were put into a 200-ml separable flask, andreacted in a nitrogen stream atmosphere at 150° C. for 4 hours. Thewater formed was removed through distillation under reduced pressure at150° C. This was cooled to 140° C. and filtered. The properties of theproducts are shown in Table 2.

EXAMPLES 29 TO 33

10% by weight of the polybutenylsuccinimide compound obtained in any ofExamples 19 to 23 was added to 500-neutral fraction mineral oil toprepare lubricant oil compositions.

The lubricant oil compositions were tested to evaluate their properties,according to the hot tube test method. The results are given in Table 3.

EXAMPLES 34 TO 38

10% by weight of the polybutenylsuccinimide compound obtained in any ofExamples 24 to 28 was added to 500-neutral fraction mineral oil toprepare lubricant oil compositions.

The lubricant oil compositions were tested to evaluate their properties,according to the hot tube test method. The results are given in Table 4.

COMPARATIVE EXAMPLES 7 TO 9

60 g of the polybutenylsuccinimide obtained in any of ProductionExamples 1 to 3, and 8 g of boric acid were put into a 200-ml separableflask, and reacted in a nitrogen stream atmosphere at 150° C. for 4hours. The water formed was removed through distillation under reducedpressure at 150° C. This was cooled to 140° C. and filtered. Theproperties of the products in Table 2.

COMPARATIVE EXAMPLES 10 to 12

10% by weight of the polybutenylsuccinimide obtained in any ofProduction Examples 1 to 3 was added to 500-neutral fraction mineral oilto prepare lubricant oil compositions.

The lubricant oil compositions were tested to evaluate their properties,according to the hot tube test method. The results are given in Table 3.

COMPARATIVE EXAMPLES 13 to 15

10% by weight of the polybutenylsuccinimide obtained in any ofComparative Examples 7 to 9 was added to 500-neutral fraction mineraloil to prepare lubricant oil compositions.

The lubricant oil compositions were tested to evaluate their properties,according to the hot tube test method. The results are given in Table 4.

TABLE 2 Kinematic Boron Base Value Viscosity at Content (mm KOH/g) 100°C. (mm²/sec) (wt. %) Production Example 1 77 149 — Production Example 285 109 — Production Example 3 98 130 — Example 19 74 141 — Example 20 71146 — Example 21 80 104 — Example 22 90 128 — Example 23 61 140 —Example 24 68 — 2.2 Example 25 65 — 2.2 Example 26 73 — 2.1 Example 2784 — 2.0 Example 28 57 — 1.8 Comparative Example 7 71 — 2.0 ComparativeExample 8 78 — 2.0 Comparative Example 9 90 — 1.9

TABLE 3 Type of Imide Hot Tube Test (270° C.) Compound Point Deposit(mg) Example 29 Example 19 7 1 or less Example 30 Example 20 7 1 or lessExample 31 Example 21 6 1 or less Example 32 Example 22 6 1 or lessExample 33 Example 23 6 1 or less Comp. Example 10 Prodn. Example 1 1 15Comp. Example 11 Prodn. Example 2 1 16 Comp. Example 12 Prodn. Example 31 19

TABLE 4 Type of Imide Hot Tube Test (270° C.) Compound Point Deposit(mg) Example 34 Example 24 10 1 or less Example 35 Example 25 10 1 orless Example 36 Example 26 9 1 or less Example 37 Example 27 9 1 or lessExample 38 Example 28 8 1 or less Comp. Example 13 Comp. Example 7 2 5Comp. Example 14 Comp. Example 8 1 5 Comp. Example 15 Comp. Example 9 19

When the data of Examples 29 to 33 are compared with those ofComparative Examples 10 to 12 in Table 3, it is understood that thelubricant oil compositions containing the succinimide compound of theinvention all gained much higher points and gave much less deposit inthe hot tube test than the conventional compositions.

When the data of Examples 34 to 38 are compared with those ofComparative Examples 13 to 15 in Table 4, the same as above shall applyalso to the lubricant oil compositions containing the succinimidecompound reacted with a boron compound, and it is understood that theborosuccinimide compounds are extremely effective.

INDUSTRIAL APPLICABILITY

The succinimide compounds and their mixtures with substitutedhydroxy-aromatic carboxylate derivatives of the invention are extremelystable even at high temperatures, and their high-temperature detergencyis extremely good. Accordingly, they are favorable for additives tolubricants and to fuel oil, and the lubricants and the fuel oilcompositions containing them are extremely good.

1. A borosuccinimide compound obtained through reaction of (a) asuccinic acid or its anhydride substituted with an alkyl or alkenylgroup having a number-average molecular weight of from 200 to 5,000, (b)a polyalkylene-polyamine of which at least 5 mol % has a terminal cyclicstructure represented by the following structural formula (1):

wherein p and q each indicates an integer of from 2 to 4, and (c) aboron compound.
 2. The borosuccinimide compound as claimed in claim 1,for which the cyclic structure-terminated polyalkylene-polyamineaccounts for from 5 to 95 mol % of all the polyalkylene-polyamine. 3.The borosuccinimide compound as claimed in claim 1, for which the cyclicstructure-terminated polyalkylene-polyamine accounts for from 10 to 90mol % of all the polyalkylene-polyamine.
 4. The borosuccinimide compoundas claimed in claim 1, for which the cyclic structure-terminatedpolyalkylene-polyamine is an aminoalkylpiperazine.
 5. Theborosuccinimide compound as claimed in claim 1, which has a boroncontent of from 0.05 to 5% by weight.
 6. A borosuccinimide compositioncomprising reacted units of (a) succinic acid substituted with an alkylor alkenyl group having a number-average molecular weight of from 200 to5,000, or an anhydride thereof, (b) a polyalkylene-polyamine of which atleast 5 mol % has a terminal cyclic structure represented by structuralformula (1):

wherein p and q each indicate an integer of from 2 to 4, and (c) a boroncompound.
 7. The borosuccinimide composition as claimed in claim 6, forwhich the cyclic structure-terminated polyalkylene-polyamine accountsfor from 5 to 95 mol % of all the polyalkylene-polyamine.
 8. Theborosuccinimide composition as claimed in claim 6, for which the cyclicstructure-terminated polyalkylene-polyamine accounts for from 10 to 90mol % of all the polyalkylene-polyamine.
 9. The succinimide compositionas claimed in claim 6, for which the cyclic structure-terminatedpolyalkylene-polyamine is an aminoalkylpiperazine.
 10. Theborosuccinimide composition as claimed in claim 6, which has a boroncontent of from 0.05 to 5% by weight.
 11. The borosuccinimidecomposition as claimed in claim 1, wherein the boron compound is atleast one selected from the group consisting of boric acid, boricanhydride, a borate, boron oxide and a boron halide.
 12. Theborosuccinimide composition as claimed in claim 6, wherein the boroncompound is at least one selected from the group consisting of boricacid, boric anhydride, a borate, boron oxide and a boron halide.
 13. Theborosuccinimide composition as claimed in claim 1, wherein the boroncompound is boric acid.
 14. The borosuccinimide composition as claimedin claim 6, wherein the boron compound is boric acid.